| Gillingham FC v Northampton Town FC 25/08/1986 | View match | |
| Gillingham FC v Bristol City FC 30/08/1986 | View match | |
| Northampton Town FC v Gillingham FC 03/09/1986 | View match | |
| Rotherham United FC v Gillingham FC 06/09/1986 | View match | |
| Gillingham FC v Middlesbrough FC 13/09/1986 | View match | |
| Gillingham FC v York City FC 16/09/1986 | View match | |
| Oxford United FC v Gillingham FC 24/09/1986 | View match | |
| Gillingham FC v Brentford FC 27/09/1986 | View match | |
| Mansfield Town FC v Gillingham FC 30/09/1986 | View match | |
| Gillingham FC v Bury FC 04/10/1986 | £5.00 | |
| Gillingham FC v Oxford United FC 07/10/1986 | View match | |
| Chester City FC v Gillingham FC 15/10/1986 | View match |